This invention relates to 2-(heterocyclic)phenyl sulfamates which are useful as agricultural chemicals.
U.S. Ser. No. 261,751 teaches that o-alkylsulfonyloxysulfamates are herbicidal.
DE No. 3,105,453 assigned to Hoechst AG teaches that phenoxysulfonylureas are herbicidal.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches the preparation of the following compounds and their use as general or selective herbicides: ##STR1## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently by hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 R.sub.2 is H, Cl, F, Br, NO.sub.2, alkyl of 1-4 carbons, alkoxy of 1-4 carbons, CF.sub.3 or ##STR6## R.sub.3 is H, Cl, F, Br, CH.sub.3, or alkoxy of 1-4 carbons; R.sub.4 is H, Cl, F, Br, NO.sub.2, alkyl of 1-4 carbons, alkoxy of 1-4 carbons, CN or ##STR7## R.sub.5 is H, Cl, F, Br, CH.sub.3, NO.sub.2 or CF.sub.3 ; R.sub.6 is H, Cl, F, Br, alkyl of 1-4 carbons or alkoxy of 1-4 carbons; PA1 R.sub.7 is Na.nu.O--, OH, or alkoxy of 1-4 carbons; PA1 X is CH.sub.3, CH.sub.3 CH.sub.2, alkoxy of 1-3 carbons, CH.sub.3 OCH.sub.2, CH.sub.3 OCH.sub.2 CH.sub.2 O, CH.sub.3 S, CH.sub.3 CH.sub.2 S, CF.sub.3 or Cl; PA1 Y is CH.sub.3, CH.sub.3 CH.sub.2, alkoxy of 1-3 carbons, CH.sub.3 OCH.sub.2, CH.sub.3 OCH.sub.2 CH.sub.2 O, CH.sub.3 S or CH.sub.2 CH.sub.3 S; and PA1 Z is CH or N; PA1 only one of R.sub.2, R.sub.3 or R.sub.4 is alkoxy; and PA1 when R.sub.5 is NO.sub.2, R.sub.4 is other than NO.sub.2. PA1 W.sub.1 is O or S; PA1 R.sub.1 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15, R.sub.16, R.sub.19, R.sub.21, R.sub.22, R.sub.23, R.sub.25 or R.sub.27 are independently H, CH.sub.3 or C.sub.2 H.sub.5 ; PA1 R.sub.6, R.sub.7, R.sub.17, R.sub.24 or R.sub.26 are independently H or CH.sub.3 ; PA1 R.sub.18 or R.sub.20 are independently H or C.sub.1 -C.sub.3 alkyl; PA1 X is Cl, CH.sub.3, OCH.sub.3, OCF.sub.2 H or SCF.sub.2 H; PA1 Y is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OC.sub.2 H.sub.5, OCH.sub.2 CF.sub.3, CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 ##STR10## or GCF.sub.2 T where G is O or S and T is H, CHClF, CHBrF, CF.sub.2 H or CHFCF.sub.3 ; and PA1 Z is CH or N; PA1 (1) Compounds of Formula I where R is H, W is O or S, and Q is Q-1 to Q-10, Q-15 and Q-16. PA1 (2) Compounds of preferred 1 where R.sub.2 l to R.sub.16, inclusive, are independently H or CH.sub.3. PA1 (3) Compounds of preferred 2 where ##STR11## (4) Compounds of preferred 2 where ##STR12## (5) Compounds of preferred 2 where ##STR13## (6) Compounds of preferred 2 where ##STR14## (7) Compounds of preferred 2 where ##STR15## (8) Compounds of preferred 2 where ##STR16## (9) Compounds of preferred 2 where ##STR17## (10) Compounds of preferred 2 where ##STR18## (11) Compounds of preferred 2 where ##STR19## (12) Compounds of preferred 2 where ##STR20## (13) Compounds of preferred 2 where ##STR21## (14) Compounds of preferred 2 where ##STR22## (15) Compounds of preferred 3 where W is O. PA1 (16) Compounds of preferred 4 where PA1 (17) Compounds of preferred 9 where PA1 (18) Compounds of preferred 2 where PA1 2-(5-isoxazolyl)phenyl N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]sulfamate; PA1 2-(5-isoxazolyl)phenyl N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]sulfamate; PA1 2-(5-isoxazolyl)phenyl N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]sulfamate; PA1 2-(5-isoxazolyl)phenyl N-[(4-methoxy-6-methyl-1,3,5-triazin-2yl)aminocarbonyl]sulfamate; PA1 2-(3-isoxazolyl)phenyl N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]sulfamate; PA1 2-(3-isoxazolyl)phenyl N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]sulfamate; PA1 2-(3-isoxazolyl)phenyl N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]sulfamate; PA1 2-(3-isoxazolyl)phenyl N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]sulfamate; PA1 2-(1,3,4-oxadiazol-2-yl)phenyl N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]sulfamate; PA1 2-(1,3,4-oxadiazol-2-yl)phenyl N-[(4methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]sulfamate; PA1 2-(1,3,4-oxadiazol-2-yl)phenyl N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]sulfamate; PA1 2-(1,3,4-oxadiazol-2-yl)phenyl N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]sulfamate; PA1 2-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]sulfamate; and PA1 2-(1,3,4-oxadiazol-2-yl)-6-methylphenyl N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]sulfamate. PA1 R.sub.16 ' is H, CH.sub.3 or C.sub.2 H.sub.5. PA1 R, R.sub.1 and R.sub.6 are as defined above. PA1 R.sub.5 is CH.sub.3 or C.sub.2 H.sub.5 ; and PA1 R.sub.4 is H, CH.sub.3 or C.sub.2 H.sub.5. PA1 R and R.sub.18 to R.sub.20 are as defined above. PA1 R.sub.14 is CH.sub.3 or C.sub.2 H.sub.5. PA1 R.sub.15 is CH.sub.3 or C.sub.2 H.sub.5. PA1 R.sub.14 is CH.sub.3 or C.sub.2 H.sub.5. PA1 R.sub.15 is H or Cl. PA1 R.sub.15 ' is H or CH.sub.3 ; and PA1 R.sub.15 is CH.sub.3 or C.sub.2 H.sub.5. PA1 R.sub.15 ' is CH.sub.3 or C.sub.2 H.sub.5. PA1 R, R.sub.26 and R.sub.27 are as defined above. PA1 (1) J. V. Metzer (ed.), Chem. Heterocyclic Compounds, 34, parts (1-3) (1978-1979). PA1 (2) J. M. Sprague and A. H. Land, "Heterocyclic Compounds", (R. C. Elderfield, ed.) V, 484-722. Wiley, New York. ##STR73## wherein R.sub.12 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 R.sub.13 is CH.sub.3 or CH.sub.2 CH.sub.3 ; and PA1 R is as defined above. ##STR74## where R.sub.12 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 R.sub.13 is CH.sub.3 or CH.sub.2 CH.sub.3 ; and PA1 R is as defined above. PA1 R.sub.9 is CH.sub.3 or CH.sub.2 CH.sub.3 ; and PA1 R is as defined above. ##STR76## wherein R.sub.8 is CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 R.sub.9 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ; and PA1 R is as defined above. PA1 R.sub.11 is CH.sub.3 or CH.sub.2 CH.sub.3 ; and PA1 R is as defined above. ##STR78## wherein R.sub.10 is CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 R.sub.11 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ; and PA1 R is as defined above. PA1 M is Cl, Br or F. PA1 R.sub.12 and R.sub.13 are H, CH.sub.3 or CH.sub.2 CH.sub.3. PA1 Y is CH(OCH.sub.3).sub.2 or ##STR83## PA1 Y is CH(OCH.sub.3).sub.2 or ##STR85## wherein X and Y are as defined in Equation 55.
French Pat. No. 1,468,747 discloses para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR2## wherein R=H, halogen, CF.sub.3 or alkyl.
Logemann et al., Chem. Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR3## wherein R is butyl, phenyl or ##STR4## and R.sub.1 is hydrogen or methyl.
When tested for hypoglycemic effect in rats (oral doeses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
U.S. Pat. No. 4,191,553 discloses herbicidal compounds of the following formula: ##STR5## wherein R.sub.1 is H, OCH.sub.3 or alkyl of 1-3 carbons;
provided that
Wojciechowski, J. Acta, Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR8## Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, soybean and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of such valuable crops by killing or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. However, the need exists for still more effective herbicides that destroy or control weeds without causing significant damage to useful crops.